diff --git a/generator/.DevConfigs/1505438c-c9a6-422f-85d8-0fa7258698f6.json b/generator/.DevConfigs/1505438c-c9a6-422f-85d8-0fa7258698f6.json
new file mode 100644
index 000000000000..0e0d465aea95
--- /dev/null
+++ b/generator/.DevConfigs/1505438c-c9a6-422f-85d8-0fa7258698f6.json
@@ -0,0 +1,9 @@
+{
+  "core": {
+    "changeLogMessages": [
+      "Update HttpRequestMessageFactory to correctly set the Content-Length header"
+    ],
+    "type": "patch",
+    "updateMinimum": true
+  }
+}
\ No newline at end of file
diff --git a/sdk/src/Core/Amazon.Runtime/Pipeline/HttpHandler/_netstandard/HttpRequestMessageFactory.cs b/sdk/src/Core/Amazon.Runtime/Pipeline/HttpHandler/_netstandard/HttpRequestMessageFactory.cs
index 4e43225ba9ff..f81f17e66ca5 100644
--- a/sdk/src/Core/Amazon.Runtime/Pipeline/HttpHandler/_netstandard/HttpRequestMessageFactory.cs
+++ b/sdk/src/Core/Amazon.Runtime/Pipeline/HttpHandler/_netstandard/HttpRequestMessageFactory.cs
@@ -625,13 +625,12 @@ public void WriteToRequestBody(HttpContent requestContent, Stream contentStream,
             if ((isChunkedUploadWrapperStreamWithLength || isTrailingHeadersWrapperStreamWithLength || isCompressionWrapperStreamWithLength)
                 || (chunkedUploadWrapperStream == null && trailingHeadersWrapperStream == null && compressionWrapperStream == null))
             {
-                long position = 0;
+                long position;
                 try
                 {
-                    if (contentStream.CanSeek)
-                    {
-                        position = contentStream.Position;
-                    }
+                    // Even in cases where the stream is unseekable the position may still be tracked due to special
+                    // circumstances of ChunkedUploadWrapperStream.
+                    position = contentStream.Position;
                 }
                 catch (NotSupportedException)
                 {
diff --git a/sdk/test/NetStandard/IntegrationTests/IntegrationTests/S3/PutObjectTests.cs b/sdk/test/NetStandard/IntegrationTests/IntegrationTests/S3/PutObjectTests.cs
index f667be23571f..01bdac2032bf 100644
--- a/sdk/test/NetStandard/IntegrationTests/IntegrationTests/S3/PutObjectTests.cs
+++ b/sdk/test/NetStandard/IntegrationTests/IntegrationTests/S3/PutObjectTests.cs
@@ -189,8 +189,10 @@ public async Task PutObjectWithoutContentEncoding(bool useChunkEncoding)
         /// <summary>
         /// Reported in https://github.com/aws/aws-sdk-net/issues/3629
         /// </summary>
-        [Fact]
-        public async Task TestResetStreamPosition()
+        [Theory]
+        [InlineData(true)]
+        [InlineData(false)]
+        public async Task TestResetStreamPosition(bool useChunkEncoding)
         {
             var memoryStream = new MemoryStream();
             long offset;
@@ -214,7 +216,7 @@ public async Task TestResetStreamPosition()
                 AutoResetStreamPosition = false,
                 AutoCloseStream = !memoryStream.CanSeek,
                 InputStream = memoryStream.CanSeek ? memoryStream : AmazonS3Util.MakeStreamSeekable(memoryStream),
-                UseChunkEncoding = false,
+                UseChunkEncoding = useChunkEncoding,
             };
 
             var putResponse = await Client.PutObjectAsync(putRequest);